Exuding self-confidence, Alan Grayson sets sights on U.S. Senate

Few people, if anyone, would describe Democrat Alan Grayson as humble — even himself or those who know him best.

Bold, bombastic, sharply intelligent, genuine even. Yes.

But not humble.

He offered a prime example recently, talking about how he believes he’s one of a rare few of the 535 members of Congress who takes the job seriously and actually gets things done and how he now wants to bring that work ethic to the U.S. Senate next year.

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“As far as I’m concerned, I’m a professional and I’m surrounded by amateurs” is how the three-term Orlando congressman put it in a recent visit with the Tampa Bay Times editorial board.

“I’m surrounded by people who do nothing, and they have a lot to be humble about. ... I feel like I’ve done a lot of good for a lot of people and I just don’t see a lot of that around me,” Grayson said. “The fact is most people in Congress are posers. If you want me to confess to some humility, I’d say: ‘Humility as compared to them?’ It would seem to me that they’re the ones that have something to answer for, not me.”

Statements like that are routinefor the lawyer, former businessman and self-made multi-millionaire who emanates self-confidence and calls himself the “congressman with guts.”

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Grayson’s bravado is matched by his colorful appearance. Walking in to any room, his 6-foot-4 stature sticks out — so does his nontraditional attire: Standard business suits accented most often by an eye-catching American flag tie and the cowboy boots that he’s rarely seen without.

A father of five, Grayson first jumped into politics a decade ago and is best known for his raw, unfiltered bluntness, sometimes to his own detriment.

Calling a female Federal Reserve lobbyist a “K-Street whore” seven years ago and once describing the Republicans’ healthcare reform plan as one that wants sick Americans to “die quickly” remain infamous moments on the congressman’s highlight reel.

Grayson quietly revels in the attention. He casually acknowledges he’s “had a hell of a life,” while frequently listing his professional and legislative accomplishments with painstaking detail — particularly his work in Congress on seniors issues and to increase healthcare research funding.

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To strike a contrast with his opponents, he’ll routinely mention how Slate (three years ago) called him “the most effective member” of Congress. Or how Business Insider (two and a half years ago) said he was among the “most productive.” Or how Time (two years ago) called him a “standout” member.

As passionately as he talks about himself, so does he defend himself. For instance, despite damning initial findings earlier this spring from an ongoing congressional ethics investigation, Grayson maintains his innocence and, instead, lays blame on political opponents who he says want only to “smear” him.

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The investigation — which is now in the hands of the House Ethics Committee — found Grayson potentially violated a litany of federal laws and ethics rules by managing once-offshore hedge funds while in office and also using his official position to attract investors to the funds.

“We’re just talking about an investment partnership between me and my five children. Even calling it a hedge fund is, to some degree, misleading,” Grayson said during one of a series of interviews with the Herald/Times. He added that if he could go back, “Would I have still invested the money? Yes.”

But his unapologetic and unabashed nature is what makes Grayson who he is: a beloved champion for Democratic progressives and a detestable annoyance for conservatives.

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“One of the many things I love about Alan is that with Alan, there’s no pretense,” said Dena Grayson, who married the congressman six weeks ago and is running to replace him in the U.S. House. “He really wears his heart on his sleeve, for better or worse. And people will sling arrows at him — but gosh, I would rather have that than have somebody who’s sort of white-washed.”

With Alan, there’s no pretense.

Dena Grayson, wife of Alan Grayson

A boy from the Bronx

The son of two teachers, Alan Mark Grayson was born March 13, 1958 in New York City.

He grew up in public housing in the Bronx and was plagued by life-threatening asthma that required him to get injections three or four times a week through his childhood, he said.

Grayson attended the Bronx High School of Science and then enrolled at Harvard College at 17 years old. He worked his way through undergraduate school in a series of jobs: night watchman, janitor and even reporter.

After three years at Harvard, Grayson graduated magna cum laude in 1978 with a self-designed major, a “special concentration” with an emphasis on urban studies.

He then went to work for the U.S. Department of Transportation in Cambridge, Mass., making $18,585 a year as an economist analyzing the effects of government policy on things like passenger travel or energy consumption, he said. It’s occupational experience he still mentions frequently, in passing, when touting his financial know-how in Congress or on the campaign trail.

Grayson has, at various times, said his time working as an economist was for either two years or four years. He said the discrepancy is simply a distinction from when he worked part-time versus full-time.

About 18 months after he started at the DOT, Grayson said he downgraded to part-time because he went back to Harvard — simultaneously continuing his economist job for about another two years while pursuing both a law degree and a master’s degree in public policy.

In four years, he had both degrees in hand. He said he would have had a Ph.D., too, but didn’t finish his dissertation.

Early professional years

After graduate school, Grayson launched his legal career, starting as a law clerk. He was an assistant to judges in both the Colorado Supreme Court and the D.C. Circuit of the U.S. Court of Appeals, where he said he served under future Supreme Court Justices Ruth Bader Ginsburg and Antonin Scalia.

“I had the benefit of literally understanding how more than a dozen different judges thought through their decision-making,” Grayson recalled.

It was during his year in Colorado that Grayson wed for the first time — although the relationship was over almost as quickly as it started.

He married Shellie Ruston in April 1984, after a swift courtship. They separated after less than a month and their marriage was formally annulled 11 months after the wedding, court records show. Ruston, who sought the annulment, could not be reached for comment.

“I just don’t know how to describe that,” Grayson said. “I wish her well but, you know, we decided to split up.”

Grayson moved to Washington, D.C., for his second clerkship in the later half of 1984 and then lived there for more than a decade.

Following his stint at the D.C. Circuit, he said Ginsburg hooked him up with a job interview at her husband’s premier law firm — Fried, Frank, Harris, Shriver & Jacobson — where Grayson specialized in government contracts law for five years.

Even at that time, Grayson showed signs of his current outspoken self and his unique sense of style, former law colleague Ira Hoffman said.

Alan has always been non-conventional.

Ira Hoffman, former law colleague

“Alan has always been non-conventional,” said Hoffman, who said he clerked briefly with Grayson in D.C., worked with him for a time at Fried Frank and later joined Grayson’s private law firm for about six years. “He is one of the sharpest people I’ve ever met and dealt with at a close level.”

While at Fried Frank in the latter half of the 1980s, Grayson helped found the Alliance for Aging Research, a nonprofit organization that Grayson says was borne from his master’s thesis about the lack of scientists researching the aging process.

Perry, who in the mid-’80s was a senior legislative staffer to California U.S. senator Alan Cranston, said in a statement last July that Grayson’s “insightful paper crossed my desk” and he later asked Grayson “to provide pro-bono legal services to get the Alliance incorporated and registered as a 501(c)(3) organization in 1986, which he did.”

Grayson served as an officer of the Alliance until he was first elected to Congress in 2008 and he speaks proudly of the group’s success.

“We got enormous increases in money for research for both gerontology and geriatrics,” Grayson said.

More jobs and marriages

1990 was another milestone year for Grayson.

He left Fried Frank to help start an international telephone services company that, along with other investments, would later make him millions. And he wed his second wife, Lolita. (The 25-year marriage was annulled last year after bitter and scandalous divorce proceedings that revealed Lolita was still married to her first husband when she wed Grayson.)

Grayson was the first president of IDT (International Discount Telecommunications), serving from 1990 to 1991. The company later went public in the mid-1990s.

In 1991, Grayson broke out on his own, starting a law firm named after himself in the D.C. suburbs of Virginia. He became nationally known in the early 2000s by suing war profiteers in Iraq under a Civil War-era law. (In 2006, “The Wall Street Journal said on its cover that I was waging a one-man war against contractor fraud in Iraq,” Grayson pointed out.)

After their first child, Skye, was born, Alan and Lolita Grayson moved to Orlando in the mid-1990s, although Grayson still spent a lot of his time in Virginia into the early 2000s.

“We were spending almost all of our vacation time in Orlando. ... I just realized at some point that I would enjoy it even more if I just lived in Orlando,” he said. “When my daughter was born we had to decide what to do, because we were starting a family, and I felt that she’d have a better childhood in Orlando, and I was right.”

Alan and Lolita Grayson would have four more children: Star, Sage and twin boys Storm and Stone. The twins, now 11, are the youngest.

Fatherhood reveals a softer side to Grayson’s sometimes-brash personality. “I always make sure to tell them frequently that I love them and often they just say the same thing, so I find that encouraging,” he said with a soft laugh.

Lolita Grayson sought her divorce in January 2014, citing an “irretrievably broken” marriage. The dispute escalated quickly and publicly, as the two traded accusations and insults openly and in court documents — including allegations by both of domestic violence. Lolita Grayson declined to comment for this story.

Alan Grayson and Dena Minning, 45, met by happenstance on a flight from Orlando to Washington, D.C., “a couple years ago,” each said. It was the only time that year that she flew out of Orlando, since she normally flew out of the Melbourne airport, she said.

Alan Grayson helped her take her bags out of the overhead bin — she’s 15 inches shorter than him — and struck up a conversation after they got off the plane, she said.

“It really became a conversation that obviously blossomed into something more, and now I’m very, very, very happy to say I’m madly in love with my best friend,” Dena Grayson said, calling him “my absolute soul-mate. He’s brilliant, he’s thoughtful, he’s totally genuine. He’s kind, he’s warm, he’s funny. That’s the Alan I know and love and same with those of us that are around him every day.”

They were engaged this spring “as soon as the annulment was final. Like, immediately,” Alan Grayson said. They were eager to wed, they said.

‘He doesn’t hold back’

The war in Iraq prompted Alan Grayson to first run for Congress in 2006.

“I took the only successful case against [war profiteers] to trial and won,” Grayson said. “It became obvious to me over time that the government was grossly mismanaging the war effort.”

Grayson’s first bid for public office failed. He credits an earlier start to his 2008 U.S. House campaign as among his reasons for victory two years later.

As a freshman representative in 2009, Grayson garnered a national reputation as a candid but polarizing figure — particularly for his remarks about Republicans’ healthcare reform plan. He described it as: “Don’t get sick. And if you do get sick, die quickly.”

Grayson was booted from office in 2010 by the tea party wave, but he won back a seat in the U.S. House after Florida’s congressional districts were redrawn in 2012.

He has notably been less explosive with his comments in his second two terms, while at the same time still gaining more national prominence thanks to frequent MSNBC appearances and a staunch progressive streak that focuses largely on social and senior issues.

“He doesn’t hold back. I think what we’ve seen is Democrats being run over — almost like a truck ran over them — because they’re afraid to speak up or speak out and say anything. And he’s not,” said Susan Smith, president of the Florida Democratic Progressive Caucus, who personally is backing Grayson in this year’s U.S. Senate contest.

But the Alan Grayson that the public sees on TV is a bit of an extreme version of himself, friends and colleagues said.

“He’s not afraid to be candid, but he’s more flamboyant on the House floor in front of CSPAN cameras than he is behind closed doors,” Hoffman said.

He brings an energy and humor but, at the same time, a recklessness that’s fun to watch.

Trial attorney John Morgan, a former Grayson supporter

Prominent Orlandotrial lawyer John Morgan supported Grayson’s political efforts in the past and said he’s still “friendly” with him, but the two are at odds now because Morgan is backing Grayson’s main rival, U.S. Rep. Patrick Murphy, in the Democratic primary on Aug. 30.

“He [Grayson] comes across to me as smart and bombastic. He’s not a fool by any stretch of the imagination. He is a very, very bright guy,” Morgan said. “He brings an energy and humor but, at the same time, a recklessness that’s fun to watch.”

Last July, before Grayson announced his campaign for Senate, Morgan tried to persuade Grayson to seek re-election because, as Morgan views it, he had a “safe seat ... but with such a presence.” He said he thinks Grayson is too liberal to garner statewide support for a Senate seat.

Grayson speaks critically of Morgan these days, accusing him of being part of the Democratic establishment that resoundingly supports Murphy in the Senate contest. Murphy has President Barack Obama, Vice President Joe Biden, Senate Minority Leader Harry Reid and myriad U.S. House and Senate members on his side — endorsements that have sparked the ire of Grayson and his progressive fan base. No member of Congress has endorsed Grayson.

“The system is rigged,” Grayson says often.

He said he wants to be a U.S. senator because “there are a lot of good things to do,” such as on Medicare and Social Security.

“When it comes to this stuff, I’m professional and I get things done for people like, literally, no one else,” he said.

▪ Experience: Grayson is in his third term in the U.S. House, currently representing Florida’s 9th Congressional District in Central Florida, including parts of Orlando. Before Congress, Grayson spent 17 years running his own law firm; he helped found an international telecommunications company and served as its first president. He also spent five years at a major D.C. law firm, and during college worked as a janitor, nightwatchman, reporter and economist.

▪ Education: Grayson graduated from the Bronx High School of Science at 17. After three years at Harvard College, he graduated in 1978 with a bachelor’s degree in “special concentration — urban studies.” He returned to Harvard University in 1979, and in 1983, he graduated with both a law degree and a master’s degree in public policy.

▪ Family: Married. Five children: Skye, Star, Sage, Storm and Stone.

▪ Net worth: Grayson’s 2015 financial disclosure won’t be available until mid-August because he filed an extension. In 2014, he reported a net worth ranging between $14 million and $105 million. Roll Call pegged his net worth closer to $34 million, making Grayson the 12th-richest member of Congress that year.

▪ Why he’s running: “I’ve mastered the rules of the House. The House is a very top-down place; the Senate is not that way. All the things I’ve done in the House I can do five times over in the Senate. ... I can’t force a vote on my bills in the House; I can force a vote on my bills in the Senate.”

Ethics investigation

In July 2015 — on the eve of Alan Grayson’s launching his U.S. Senate campaign — a conservative watchdog group, called Foundation for Accountability & Civic Trust, and St. Lucie County Democratic Party Chairwoman Celeste Bush filed complaints with the Office of Congressional Ethics. They accused the Orlando Democratic congressman of violating ethics rules by using his official position to make money from personal hedge funds he managed, including two based in the Cayman Islands.

At the time and since then, Grayson has staunchly proclaimed his innocence, calling the complaints unfounded and a political “smear.” (Bush supports Grayson’s Democratic rival in the Senate race, U.S. Rep. Patrick Murphy.)

Media, including the Tampa Bay Times, reported in detail about Grayson’s hedge funds for several months, but the most explosive revelations came in a February 2016 New York Times story that said Grayson “told potential investors in his hedge fund that they should contribute money to the fund to capitalize on the unrest he observed around the world, and to take particular advantage when there was ‘blood in the streets.’ ”

Grayson refuted the blistering report, but it prompted Senate Minority Leader Harry Reid, the next day, to call on Grayson to drop out of the U.S. Senate race because his actions “disgrace the halls of Congress.”

The Office of Congressional Ethics released its findings in April, flagging a number of potential violations of federal law and congressional ethics rules. Among them, investigators found Grayson ran a hedge fund that improperly used his name, a congressional staffer for Grayson also worked for his hedge fund, Grayson had numerous “significant” omissions on his financial disclosure forms and he improperly mixed political and official work by participating in press interviews about his U.S. Senate campaign from his congressional office.

Grayson disputes the findings and contends the investigation is over because the OCE didn’t create an investigative subcommittee. However, the probe remains open; it is up to the House Ethics Committee to further investigate, if its members choose to do so.